C5'- and C3'-sugar radicals produced via photo-excitation of one-electron oxidized adenine in 2'-deoxyadenosine and its derivatives

Nucleic Acids Research
Amitava AdhikaryMichael D Sevilla

Abstract

We report that photo-excitation of one-electron-oxidized adenine [A(-H)*] in dAdo and its 2'-deoxyribonucleotides leads to formation of deoxyribose sugar radicals in remarkably high yields. Illumination of A(-H)* in dAdo, 3'-dAMP and 5'-dAMP in aqueous glasses at 143 K leads to 80-100% conversion to sugar radicals at C5' and C3'. The position of the phosphate in 5'- and 3'-dAMP is observed to deactivate radical formation at the site of substitution. In addition, the pH has a crucial influence on the site of sugar radical formation; e.g. at pH approximately 5, photo-excitation of A(-H)* in dAdo at 143 K produces mainly C5'* whereas only C3'* is observed at high pH approximately 12. 13C substitution at C5' in dAdo yields 13C anisotropic couplings of (28, 28, 84) G whose isotropic component 46.7 G identifies formation of the near planar C5'*. A beta-13C 16 G isotropic coupling from C3'* is also found. These results are found to be in accord with theoretically calculated 13C couplings at C5' [DFT, B3LYP, 6-31(G) level] for C5'* and C3'*. Calculations using time-dependent density functional theory [TD-DFT B3LYP, 6-31G(d)] confirm that transitions in the near UV and visible induce hole transfer from the base radical to the sugar grou...Continue Reading

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Citations

May 7, 2010·Chemical Reviews·Anil Kumar, Michael D Sevilla
Feb 1, 2013·Journal of the American Chemical Society·Amitava AdhikaryMichael D Sevilla
May 28, 2009·Journal of the American Chemical Society·Amitava AdhikaryMichael D Sevilla
Nov 28, 2006·The Journal of Physical Chemistry. B·Anil Kumar, Michael D Sevilla
Jun 6, 2007·The Journal of Physical Chemistry. B·Amitava AdhikaryMichael D Sevilla
May 5, 2012·The Journal of Physical Chemistry. B·Amitava AdhikaryMichael D Sevilla
Oct 12, 2012·Chemical Research in Toxicology·Amy R JonesEdward J Merino
Oct 9, 2014·Journal of the American Chemical Society·Amitava AdhikaryMichael D Sevilla
May 16, 2013·Physical Chemistry Chemical Physics : PCCP·Siv G AalbergsjøEinar Sagstuen
Nov 24, 2016·FEBS Letters·Lorenz HeidingerErik Schleicher
Jan 1, 2010·Physical Chemistry Chemical Physics : PCCP·Amitava AdhikaryMichael D Sevilla
Oct 18, 2020·Nature Communications·Alexandra StützerHenning Urlaub
Feb 13, 2021·International Journal of Molecular Sciences·Michael BellMichael D Sevilla
Mar 15, 2011·The Journal of Physical Chemistry. C, Nanomaterials and Interfaces·Ilya A ShkrobMichael D Sevilla
Jan 30, 2008·The Journal of Physical Chemistry. B·Deepti KhanduriMichael D Sevilla

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Methods Mentioned

BETA
ESR
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Software Mentioned

ESRADSUB
ESRPLAY
Gaussian
Gaussview

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